CZ20022465A3 - Substituované benzoylguanidiny, způsob jejich přípravy, jejich pouľití jako léčiva nebo diagnostika, a léčivo, které je obsahuje - Google Patents

Substituované benzoylguanidiny, způsob jejich přípravy, jejich pouľití jako léčiva nebo diagnostika, a léčivo, které je obsahuje Download PDF

Info

Publication number: CZ20022465A3
Authority: CZ; Czechia
Prior art keywords: group; hydrogen; alkyl; medicament; preparation
Prior art date: 2000-01-19

Application number

CZ20022465A

Other languages

Czech (cs)

English (en)

Inventor

Andreas Weichert

Udo Albus

Hans-Willi Jansen

Heinz-Werner Kleemann

Hans-Jochen Lang

Original Assignee

Aventis Pharma Deutschland Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-01-19

Filing date

2001-01-08

Publication date

2002-10-16

2001-01-08 Application filed by Aventis Pharma Deutschland Gmbh filed Critical Aventis Pharma Deutschland Gmbh

2002-10-16 Publication of CZ20022465A3 publication Critical patent/CZ20022465A3/cs

Links

239000003814 drug Substances 0.000 title claims abstract description 35
AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title claims description 27
238000000034 method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 4
239000000032 diagnostic agent Substances 0.000 title 1
229940039227 diagnostic agent Drugs 0.000 title 1
-1 methoxy, hydroxy, amino, methylamino, dimethylamino Chemical group 0.000 claims abstract description 31
238000011282 treatment Methods 0.000 claims abstract description 25
229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
229910052731 fluorine Inorganic materials 0.000 claims abstract description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 20
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 17
238000011321 prophylaxis Methods 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 9
208000028867 ischemia Diseases 0.000 claims abstract description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
206010002383 Angina Pectoris Diseases 0.000 claims abstract description 3
229910052740 iodine Inorganic materials 0.000 claims abstract description 3
206010003119 arrhythmia Diseases 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 63
239000001257 hydrogen Substances 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 38
125000001153 fluoro group Chemical group F* 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000001309 chloro group Chemical group Cl* 0.000 claims description 18
239000000460 chlorine Chemical group 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
201000010099 disease Diseases 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
238000002560 therapeutic procedure Methods 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
210000000056 organ Anatomy 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
230000000302 ischemic effect Effects 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
208000010125 myocardial infarction Diseases 0.000 claims description 4
125000001425 triazolyl group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
230000035939 shock Effects 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
238000001356 surgical procedure Methods 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
210000003169 central nervous system Anatomy 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
239000011630 iodine Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
238000004321 preservation Methods 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000006793 arrhythmia Effects 0.000 claims 1
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230000004060 metabolic process Effects 0.000 claims 1
210000001428 peripheral nervous system Anatomy 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
206010061216 Infarction Diseases 0.000 abstract description 4
230000007574 infarction Effects 0.000 abstract description 4
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
230000003293 cardioprotective effect Effects 0.000 abstract description 2
230000035778 pathophysiological process Effects 0.000 abstract description 2
230000007547 defect Effects 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
239000002904 solvent Substances 0.000 description 14
239000002253 acid Substances 0.000 description 10
230000002265 prevention Effects 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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239000003112 inhibitor Substances 0.000 description 5
208000035150 Hypercholesterolemia Diseases 0.000 description 4
208000031226 Hyperlipidaemia Diseases 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
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150000002632 lipids Chemical class 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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108010007622 LDL Lipoproteins Proteins 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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150000007513 acids Chemical class 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
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238000002474 experimental method Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000000055 hyoplipidemic effect Effects 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
WADVPTOCPSBYLX-UHFFFAOYSA-N 4-(2-imidazol-1-ylphenoxy)-2-methyl-5-(trifluoromethyl)benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(OC=2C(=CC=CC=2)N2C=NC=C2)=C1C(F)(F)F WADVPTOCPSBYLX-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
206010003225 Arteriospasm coronary Diseases 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
208000007530 Essential hypertension Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
GRXSDEMBBAEEOH-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-[2-(triazol-1-yl)phenoxy]-5-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=C(C(=O)N=C(N)N)C(C)=CC(OC=2C(=CC=CC=2)N2N=NC=C2)=C1C(F)(F)F GRXSDEMBBAEEOH-UHFFFAOYSA-N 0.000 description 2
TZDUYNJFMQURCD-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2-imidazol-1-ylphenoxy)-2-methyl-5-(trifluoromethyl)benzamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)NC(N)=N)C(C)=CC(OC=2C(=CC=CC=2)N2C=NC=C2)=C1C(F)(F)F TZDUYNJFMQURCD-UHFFFAOYSA-N 0.000 description 2
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125000003373 pyrazinyl group Chemical group 0.000 description 2
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
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CYKCUAPYWQDIKR-UHFFFAOYSA-N 4-(1h-imidazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1C=NC=C1 CYKCUAPYWQDIKR-UHFFFAOYSA-N 0.000 description 1
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150000001502 aryl halides Chemical class 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
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201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
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230000000747 cardiac effect Effects 0.000 description 1
230000001269 cardiogenic effect Effects 0.000 description 1
230000001364 causal effect Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000009693 chronic damage Effects 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
208000019425 cirrhosis of liver Diseases 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000006880 cross-coupling reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
235000018823 dietary intake Nutrition 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000132 electrospray ionisation Methods 0.000 description 1
230000003511 endothelial effect Effects 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
230000003176 fibrotic effect Effects 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
208000020346 hyperlipoproteinemia Diseases 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
230000003902 lesion Effects 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
229960004844 lovastatin Drugs 0.000 description 1
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
230000004066 metabolic change Effects 0.000 description 1
QWEWOEMUGDJXBR-UHFFFAOYSA-N methyl 2-methyl-4-[2-(triazol-1-yl)phenoxy]-5-(trifluoromethyl)benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(C(F)(F)F)=C1OC1=CC=CC=C1N1N=NC=C1 QWEWOEMUGDJXBR-UHFFFAOYSA-N 0.000 description 1
XUAPMUNNKKKKJF-UHFFFAOYSA-N methyl 4-(2-imidazol-1-ylphenoxy)-2-methyl-5-(trifluoromethyl)benzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(C(F)(F)F)=C1OC1=CC=CC=C1N1C=NC=C1 XUAPMUNNKKKKJF-UHFFFAOYSA-N 0.000 description 1
GEISXGJCBRQRRD-UHFFFAOYSA-N methyl 4-fluoro-2-methyl-3-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(F)C(C(F)(F)F)=C1C GEISXGJCBRQRRD-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008249 pharmaceutical aerosol Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
230000004224 protection Effects 0.000 description 1
239000011251 protective drug Substances 0.000 description 1
230000009993 protective function Effects 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000054 salidiuretic effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000009441 vascular protection Effects 0.000 description 1
210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Diabetes (AREA)
Obesity (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Biomedical Technology (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Surgery (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Reproductive Health (AREA)
Gastroenterology & Hepatology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

CZ20022465A 2000-01-19 2001-01-08 Substituované benzoylguanidiny, způsob jejich přípravy, jejich pouľití jako léčiva nebo diagnostika, a léčivo, které je obsahuje CZ20022465A3 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10001879A DE10001879A1 (de)	2000-01-19	2000-01-19	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (1)

Publication Number	Publication Date
CZ20022465A3 true CZ20022465A3 (cs)	2002-10-16

Family

ID=7627855

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20022465A CZ20022465A3 (cs)	2000-01-19	2001-01-08	Substituované benzoylguanidiny, způsob jejich přípravy, jejich pouľití jako léčiva nebo diagnostika, a léčivo, které je obsahuje

Country Status (26)

Country	Link
US (1)	US6703411B2 (de)
EP (1)	EP1259481B1 (de)
JP (1)	JP4880849B2 (de)
KR (1)	KR100726701B1 (de)
CN (1)	CN1184196C (de)
AR (1)	AR027237A1 (de)
AT (1)	ATE530518T1 (de)
AU (1)	AU780466B2 (de)
BR (1)	BR0107660A (de)
CA (1)	CA2397531A1 (de)
CZ (1)	CZ20022465A3 (de)
DE (1)	DE10001879A1 (de)
EE (1)	EE200200381A (de)
HR (1)	HRP20020592A2 (de)
HU (1)	HUP0204095A3 (de)
IL (1)	IL150740A0 (de)
MX (1)	MXPA02006431A (de)
NO (1)	NO20023383L (de)
NZ (1)	NZ520213A (de)
PL (1)	PL356589A1 (de)
RU (1)	RU2267486C2 (de)
SK (1)	SK10382002A3 (de)
TW (1)	TWI240718B (de)
WO (1)	WO2001053256A1 (de)
YU (1)	YU52202A (de)
ZA (1)	ZA200205696B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10204989A1 (de) *	2002-02-07	2003-08-21	Aventis Pharma Gmbh	Dihydro-thia-phenanthren-carbonyl-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
US20050124666A1 (en)	2003-11-13	2005-06-09	Aventis Pharma Deutschland Gmbh	Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE158278T1 (de) *	1992-02-15	1997-10-15	Hoechst Ag	Ortho-substituierte benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltendes medikament
JP2689058B2 (ja) *	1992-11-02	1997-12-10	新日本製鐵株式会社	塗装体の乾燥・焼付装置
DE4325822A1 (de) *	1993-07-31	1995-02-02	Hoechst Ag	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4328869A1 (de) *	1993-08-27	1995-03-02	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4430861A1 (de) *	1994-08-31	1996-03-07	Merck Patent Gmbh	Heterocyclyl-benzoylguanidine
DE4430916A1 (de)	1994-08-31	1996-03-07	Merck Patent Gmbh	Alkyl-benzoylguanidin-Derivate
DE19529612A1 (de) *	1995-08-11	1997-02-13	Merck Patent Gmbh	Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate
DE19608161A1 (de) *	1996-03-04	1997-09-11	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19621319A1 (de) *	1996-05-28	1997-12-04	Hoechst Ag	Bis-ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19624178A1 (de)	1996-06-18	1998-01-08	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

2000
- 2000-01-19 DE DE10001879A patent/DE10001879A1/de not_active Withdrawn
2001
- 2001-01-08 HR HR20020592A patent/HRP20020592A2/hr not_active Application Discontinuation
- 2001-01-08 MX MXPA02006431A patent/MXPA02006431A/es active IP Right Grant
- 2001-01-08 CN CNB018038247A patent/CN1184196C/zh not_active Expired - Fee Related
- 2001-01-08 EE EEP200200381A patent/EE200200381A/xx unknown
- 2001-01-08 HU HU0204095A patent/HUP0204095A3/hu unknown
- 2001-01-08 WO PCT/EP2001/000137 patent/WO2001053256A1/de not_active Ceased
- 2001-01-08 PL PL01356589A patent/PL356589A1/xx not_active Application Discontinuation
- 2001-01-08 AT AT01900139T patent/ATE530518T1/de active
- 2001-01-08 YU YU52202A patent/YU52202A/sh unknown
- 2001-01-08 BR BR0107660-4A patent/BR0107660A/pt not_active IP Right Cessation
- 2001-01-08 JP JP2001553261A patent/JP4880849B2/ja not_active Expired - Fee Related
- 2001-01-08 RU RU2002122089/04A patent/RU2267486C2/ru not_active IP Right Cessation
- 2001-01-08 CZ CZ20022465A patent/CZ20022465A3/cs unknown
- 2001-01-08 IL IL15074001A patent/IL150740A0/xx unknown
- 2001-01-08 KR KR1020027009256A patent/KR100726701B1/ko not_active Expired - Fee Related
- 2001-01-08 SK SK1038-2002A patent/SK10382002A3/sk not_active Application Discontinuation
- 2001-01-08 NZ NZ520213A patent/NZ520213A/en unknown
- 2001-01-08 AU AU23732/01A patent/AU780466B2/en not_active Ceased
- 2001-01-08 EP EP01900139A patent/EP1259481B1/de not_active Expired - Lifetime
- 2001-01-08 CA CA002397531A patent/CA2397531A1/en not_active Abandoned
- 2001-01-17 US US09/760,670 patent/US6703411B2/en not_active Expired - Fee Related
- 2001-01-17 TW TW090100987A patent/TWI240718B/zh not_active IP Right Cessation
- 2001-01-17 AR ARP010100207A patent/AR027237A1/es unknown
2002
- 2002-07-12 NO NO20023383A patent/NO20023383L/no not_active Application Discontinuation
- 2002-07-17 ZA ZA200205696A patent/ZA200205696B/xx unknown

Also Published As

Publication number	Publication date
AR027237A1 (es)	2003-03-19
NO20023383L (no)	2002-09-03
IL150740A0 (en)	2003-02-12
EP1259481A1 (de)	2002-11-27
KR20020073175A (ko)	2002-09-19
YU52202A (sh)	2006-01-16
AU2373201A (en)	2001-07-31
HRP20020592A2 (en)	2004-08-31
NO20023383D0 (no)	2002-07-12
BR0107660A (pt)	2002-11-19
US20010016596A1 (en)	2001-08-23
CA2397531A1 (en)	2001-07-26
HK1051853A1 (en)	2003-08-22
RU2267486C2 (ru)	2006-01-10
EE200200381A (et)	2003-12-15
HUP0204095A2 (hu)	2003-04-28
ZA200205696B (en)	2003-11-26
ATE530518T1 (de)	2011-11-15
RU2002122089A (ru)	2004-01-10
MXPA02006431A (es)	2002-11-29
WO2001053256A1 (de)	2001-07-26
CN1395558A (zh)	2003-02-05
KR100726701B1 (ko)	2007-06-13
CN1184196C (zh)	2005-01-12
US6703411B2 (en)	2004-03-09
SK10382002A3 (sk)	2003-04-01
EP1259481B1 (de)	2011-10-26
JP2003520267A (ja)	2003-07-02
AU780466B2 (en)	2005-03-24
DE10001879A1 (de)	2001-07-19
HUP0204095A3 (en)	2005-05-30
NZ520213A (en)	2004-08-27
JP4880849B2 (ja)	2012-02-22
PL356589A1 (en)	2004-06-28
TWI240718B (en)	2005-10-01

Publication	Publication Date	Title
RU2160727C2 (ru)	2000-12-20	Бензоилгуанидины, способ их получения, промежуточное соединение для их получения, способ ингибирования и лекарственное средство
SI9500211A (en)	1996-02-29	Ortho-amino-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic as well as medicament containing them
RU2165412C2 (ru)	2001-04-20	Бензоилгуанидины, способ их получения, способ ингибирования, фармацевтический состав и способ его получения
RU2214397C2 (ru)	2003-10-20	Ортозамещенные бензоилгуанидины и лекарственное средство на их основе
RU2267486C2 (ru)	2006-01-10	Бензоилгуанидины, способ их получения, содержащие их лекарственные средства, а также способ лечения и профилактики заболеваний
KR100498799B1 (ko)	2005-12-16	오르토-치환된벤조일구아니딘,이의제조방법및이를포함하는약제학적조성물
CZ290027B6 (cs)	2002-05-15	Benzoylguanidin, jeho použití jako léčivo a léčivo tento benzoylguanidin obsahující
SI9500362A (en)	1996-06-30	Substituted benzoyl guanidines, process for the preparation thereof, use thereof as a medicine or as a diagnostic agent as well as a medicine containing them
SK66997A3 (en)	1997-12-10	Substituted 1-naphtoylguanidines, producing method thereof, their use as a drug or diagnostic agent, as well as drug containing the same
CZ20021218A3 (cs)	2002-06-12	Heterocyklicky substituované benzoylguanidiny, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje
SK66497A3 (en)	1997-12-10	Bis-ortho-substituted benzoylguanidines, manufacturing process thereof, their us as a drug or diagnostic agent, as well as drug containing the same
SK23797A3 (en)	1997-11-05	Ortho-substituted benzoylguanidines, producing method, their use as a drug or diagnostic agent, as well as a drug containing the same
SK148796A3 (en)	1997-10-08	Diguanides of subsituted benzenedicarboxylic acids, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing them
SK27597A3 (en)	1997-11-05	Ortho-substituted benzoylguanidines, preparation method thereof, their use as a drug or diagnostic agent, as well as a drug containing the same
CZ97698A3 (cs)	1998-11-11	Ortho-substituované benzoylguanidiny, způsob jejich přípravy, léčivo, které je obsahuje, a jejich použití
RS52202B (sr)	2012-10-31	Postupak za dobijanje supstituisanih ariloksi-2,3- epoksipropana
MXPA96005675A (en)	1997-08-01	Diguanididas of bencenodicarboxilicos substitute acids, procedure for its preparation, its employment as a diagnostic medicine or agent, as well as a medication that the